Esperanza and Irwin have a story to tell. As scandalous ancestors go, Col. Henry Huddleston Rogers II would have been enough for most families. But then he had a daughter. The colonel’s namesake father, a partner in Standard Oil and noted “robber baron” of the Gilded Age, was one of the wealthiest men of his day. Amassing an estimated $100 million fortune, Rogers senior also acquired the nickname“Hell Hound” for his rapacious ways. It was meant as a compliment. Alas, young Harry was spoiled by his father’s money. As he aged into adulthood, after receiving his inheritance in 1910, various sources describe him as ruthless, or a bully, or a ruthless bully.In 1914 he used some of the money to build Black Point, the family’s summer estate inSouthampton, also known as the “Beach House,” adding a hunting lodge in nearby North Sea in the 1920s. The colonel commissioned John Russell Pope*, the architect responsible for the National Gallery of Art in Washington, D.C., to design his shooting box overlooking Scallop Pond. The Sag Harbor Express reported that, at the time, it “encompassed 2,000 acres on both sides of the pond and was the largest privately-owned estate on Long Island.” By all accounts, the Port of Missing Men (as it was dubbed) offered the proverbial good time that was had by all. One rumor is that he had duck blinds installed on the water that were wired directly to Wall Street. The colonel’s guests were able to remain unreachable to their wives but connected to the trading floor. Meanwhile, during Prohibition, there was a major liquor drop-off point conveniently close by, at the end of North Sea Road. Later, the drop-off point would become a notorious cathouse. The colonel and his wife, the former Mary Benjamin, had a daughter in 1902: Mary Millicent Abigail Rogers. The artistically inclined Millicent would go on to run through three husbands,plus Clark Gable. In 2011, her rich life became the subject of a biography, Searching for Beauty: The Life of Millicent Rogers, the American Heiress Who Taught the World About Style, by Cherie Burns. Listening is believing!
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